Uscharidin

Details

• Internal ID: 78747fd5-cf97-4988-9f47-4264e5391cc4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
• SMILES (Canonical): CC1CC(=O)C2(C(O1)OC3CC4CCC5C(C4(CC3O2)C=O)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O
• SMILES (Isomeric): C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3C[C@@H]4CC[C@@H]5[C@@H]([C@]4(C[C@H]3O2)C=O)CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O
• InChI: InChI=1S/C29H38O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-22,25,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,25+,26-,27-,28+,29+/m1/s1
• InChI Key: YOCULAYFPPWLRI-OLEQQPCLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₉
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.25158279 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEBI:9913
• 24321-47-9
• 2GU13C5298
• (1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
• USCHARIDIN [MI]
• C08883
• CHEMBL449207
• SCHEMBL2207486
• UNII-2GU13C5298
• DTXSID30947156
• BDBM50277172
• 4-18-00-03125 (Beilstein Handbook Reference)
• Q27108515
• (2.ALPHA.,3.BETA.,5.ALPHA.)-14-HYDROXY-19-OXO-2,3-(((2S,3R,6R)-TETRAHYDRO-3-HYDROXY-6-METHYL-4-OXO-2H-PYRAN-3,2-DIYL)BIS(OXY))CARD-20(22)-ENOLIDE
• (3bbeta,5aalpha,6aalpha,7abeta,12abeta,13balpha)-3abeta,11abeta-Dihydroxy-9alpha,15abeta-dimethyl-11-oxo-1beta-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-9H,13aH-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxin-13abeta-carbaldehyde
• 3a,11a-Dihydroxy-9,15a-dimethyl-11-oxo-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-7aH,13aH-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-13a-carbaldehyde
• 5.alpha.-Card-20(22)-enolide, 2.alpha.,14-dihydroxy-19-oxo-3.beta.-[(tetrahydro-6-methyl-3,4-dioxo-2H-pyran-2-yl)oxy]-
• CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3R,6R)-TETRAHYDRO-3-HYDROXY-6-METHYL-4-OXO-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2.ALPHA.,3.BETA.,5.ALPHA.)-
• Card-20(22)-enolide, 2,14-dihydroxy-19-oxo-3-[(tetrahydro-6-methyl-2,3-dioxo-2H-pyran-2-yl)oxy]-, [2.alpha.,3.beta.(2S,6R),5.alpha.]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.7835	78.35%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8863	88.63%
OATP2B1 inhibitior	-	0.7125	71.25%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7816	78.16%
BSEP inhibitior	+	0.8450	84.50%
P-glycoprotein inhibitior	+	0.6073	60.73%
P-glycoprotein substrate	+	0.7250	72.50%
CYP3A4 substrate	+	0.7078	70.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8417	84.17%
CYP2C9 inhibition	-	0.9339	93.39%
CYP2C19 inhibition	-	0.9607	96.07%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.9318	93.18%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9597	95.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4425	44.25%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9434	94.34%
Skin irritation	+	0.5614	56.14%
Skin corrosion	-	0.9206	92.06%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6517	65.17%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5824	58.24%
skin sensitisation	-	0.9086	90.86%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5845	58.45%
Acute Oral Toxicity (c)	I	0.8375	83.75%
Estrogen receptor binding	+	0.8057	80.57%
Androgen receptor binding	+	0.8188	81.88%
Thyroid receptor binding	-	0.5142	51.42%
Glucocorticoid receptor binding	+	0.7395	73.95%
Aromatase binding	+	0.6702	67.02%
PPAR gamma	+	0.5415	54.15%
Honey bee toxicity	-	0.7554	75.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9821	98.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.28%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.16%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.10%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.23%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	91.99%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.91%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.90%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.54%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.78%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.40%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.34%	97.14%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.96%	91.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.72%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.91%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.30%	92.94%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Asclepias subulata
• Calotropis procera
• Gomphocarpus fruticosus
• Hyperbaena columbica
• Thymus vulgaris
• Viburnum lantanoides

Cross-Links

• PubChem: 441874
• NPASS: NPC171619
• ChEMBL: CHEMBL449207
• LOTUS: LTS0225602
• wikiData: Q27108515